Pineapple Upside Down Cupcakes

(Last Updated On: August 4, 2020)

Pineapple Upside Down Cupcakes: Tender vanilla cake topped with a rich caramel sauce and  juicy fruit.  If you like the cake you’ll go crazy over the cupcakes!

pineapple upside down cupcakes

If you like pineapple you may also enjoy my Pina Colada Poke Cake and Pineapple Margaritas

Pineapple upside down cake is one of those recipes that is just a classic. My Grandma made it often when I was growing up.

Sometimes, instead of making a full sized pineapple upside down cake, I like to make pineapple upside down cake cupcakes. These are mine versions of the classic. All that great flavor, but easier and quicker to make. Plus you don’t have to worry about flipping a huge cake over!

Making mini pineapple upside down cakes is great for a crowd. People will love having their own little dessert! Great for potlucks and birthdays too. No one will ever guess how easy they are! For an extra special treat serve with whipped cream, or vanilla ice cream.


pineapple upside down cupcakes recipe

What Is Pineapple Upside Down Cake?

Pineapple upside down cake starts with a fluffy vanilla cake batter. On the bottom of the cake pan butter, brown sugar, cherries, and of course pineapple are added. Then the cake batter is added on top. Once the cake is baked and cooled, it is turned out of the pan so that the pineapple and cherry are on top. It is called upside down cake as you are baking the top of the cake on the bottom of the pan. We follow the same exact process for these best pineapple upside down cupakes.

pineapple upside down cake cupcakes

Pineapple Upside Down Cupcakes Ingredients

Homemade Cakes: You can always use a cake mix, but I like to make my pineapple upside down cupcakes from scratch.

  • Flour, Baking  Powder ,and Salt
  • White Sugar
  • Butter
  • Vanilla
  • Egg
  • Milk: Use whole milk for the best results.

For the Topping

  • Pineapple Slices: Be sure to drain these in a strainer. You could also use fresh pineapple if you prefer.
  • Maraschino Cherries
  • Brown Sugar
  • Butter

mini pineapple upside down cake

Pineapple Upside Down Cupcake Recipe

  1. Prep Work: Preheat oven to 350 degrees F. Spray muffin tins with non stick baking spray.
  2. For the Topping: In a medium bowl, combine melted butter and brown sugar. Evenly divide between prepared muffin tins.  Add one pineapple slice and a cherry to each as well.
  3. Dry Ingredients:  In a large bowl, combine flour, salt, and baking powder.
  4. Cream Butter: In another large bowl, cream butter and sugar until light and fluffy. Add in vanilla and eggs.
  5. Alternate flour mixture and milk until everything is just combined.
  6. Bake: Evenly divide between muffin wells. Bake for 18-22 minutes. Cool and flip over to remove.

mini pineapple upside down cake recipe

Frequently Asked Questions


Can You Freeze Mini Pineapple Upside Down Cakes?

You can freeze pineapple upside down cake cupcakes. In order to freeze these treats, first freeze them individually and uncovered for an hour. Then, wrap each mini cake and freeze. Don’t skip freezing them individually first, or the yummy topping could get stuck to the plastic wrap. Thaw in the fridge before enjoying.

Does Pineapple Upside Down Cake Need To Be Refrigerated?

When making pineapple upside down cake or cupcakes I store them in the fridge to keep the fruit fresh.  Store in a sealed container for up to 3-5 days.

Can You Make Them Ahead?

While this pineapple upside down cupcake recipe will taste great even if it is made ahead of time, it does not look as nice.  The fruit can sink into the cake or fall off. I suggest making the day of if possible.

More Cupcakes I Love

German Chocolate Cupcakes

Easy Margarita Cupcakes

Hi Hat Cupcakes

pineapple upside down cupcakes

Pineapple Upside Down Cupcakes

Tender vanilla cake topped with a rich caramel sauce and  juicy fruit.  If you like the cake you'll go crazy over the cupcakes!
Course Dessert
Cuisine American
Keyword Birthday, How To Make Pineapple Upside Down Cupcakes, Pineapple Upside Down Cupcake Recipe, Pineapple Upside Down Cupcakes
Prep Time 15 minutes
Cook Time 18 minutes
Total Time 33 minutes
Servings 12 Cupcakes
Calories 410kcal
Follow On Pinterest For More Recipe IdeasFollow @bakingbeautyblog or #bakingbeautyblog
Pin Recipe


For the Topping

  • 2 20 Ounce Cans Pineapple Slices
  • 1 Jar Maraschino Cherries
  • 2/3 Cup Brown Sugar Packed
  • 4 Tablespoons Butter Melted

For the Cakes

  • 2 1/2 Cups All Purpose Flour
  • 1 1/3 Cup White Sugar
  • 2 1/2 Teaspoons Baking Powder
  • 1/4 Teaspoon Salt
  • 3/4 Cup Butter Softened
  • 1 Teaspoon Vanilla
  • 3 Eggs
  • 1 1/4 Cups Milk


  • Preheat oven to 350 degrees F. Spray muffin tin with non stick baking spray. 
  • In a medium bowl, combine brown sugar and melted butter. Divide between muffin tins. Also, add one pineapple slice and one cherry to each. 
  • In a large bowl, combine flour, salt, and baking powder. 
  • In another large bowl, cream butter and sugar until light and fluffy. Add vanilla, and eggs one at a time. 
  • Alternate adding in flour mixture and milk until everything is just combined.  
  • Divide evenly between prepared pans.  Bake for 18-22 minutes. 
  • Cool before flipping over. 


Calories: 410kcal | Carbohydrates: 61g | Protein: 5g | Fat: 16g | Saturated Fat: 10g | Cholesterol: 81mg | Sodium: 214mg | Potassium: 186mg | Fiber: 1g | Sugar: 40g | Vitamin A: 590IU | Calcium: 99mg | Iron: 1.6mg
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